1,2-dichloro-3,3,3-trifluoropropene includes an unsaturated bond, and is expected to provide a function of a cleaner or a coolant as hydrochlorofluorocarbon (HCFC), which is relatively easily decomposed in the atmosphere.
There are various known methods for producing 1,2-dichloro-3,3,3-trifluoropropene. For example, A. L. Henne et al., J. Am. Chem. Soc., 1941, pp. 3478-3479 discloses a method of reacting 1,2,3,3,3-pentachloropropene with antimony trifluoride in a liquid phase.
A. M. Whaley et al., J. Am. Chem. Soc., 1948, pp. 1026-1027 discloses a method of reacting 1,1,2,3,3-pentachloropropene and antimony trifluoride with adding antimony pentachloride in a liquid phase. R. N. Haszeldine et al., J. Chem. Soc., 1951, pp 2495-2504 discloses a method of adding potassium hydroxide in a solid state to 1,2,2,-trichloro-3,3,3-trifluoropropane in a liquid state and refluxing, while heating, the resultant substance to produce 1,2-dichloro-3,3,3-trifluoropropene.
Regarding a reaction of 1,2-dichloro-3,3,3-trifluoropropene, U.S. Pat. No. 2,739,987 discloses that a reaction of 1,2-dichloro-3,3,3-trifluoropropene with methanol in the presence of potassium hydroxide generates 1-chloro-2-methoxy-3,3,3-trifluoropropene.
WO2012/112827 discloses that a reaction of 1,2-dichloro-3,3,3-trifluoropropene with a base generates 1-chloro-3,3,3-trifluoropropyne.
According to the production method described in R. N. Haszeldine et al., J. Chem. Soc., 1951, pp 2495-2504, powdery potassium hydroxide is dispersed in 1,2,2-trichloro-3,3,3-trifluoropropane in a liquid state to cause a reaction. However, the yield is low (48%) and the reaction is not uniform. Therefore, this method is not considered to be efficient as an industrial production method.
As can be seen from the above, it has been desired to establish a method for producing 1,2-dichloro-3,3,3-trifluoropropene, which is a target compound of the present invention, easily and in an industrial scale.